(S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol Chemical Properties

Boiling point:

379.5±42.0 °C(Predicted)

Density 

1.616±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.57±0.20(Predicted)

(S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol Usage And Synthesis

Synthesis

To a stirred solution of 2,5-dibromopyridine (1.0 g, 4.2 mmol) in tert-butanol (5 ml) was added (S)-3-hydroxypyrrolidine (0.74 g, 8.44 mmol; Aldrich) and sodium carbonate (1.34 g, 12.70 mmol). The reaction mixture was placed in a reaction flask and heated to reflux at 140 °C for 3 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with water (20 ml) and subsequently extracted with ethyl acetate (20 ml). The aqueous phase was separated and the extraction was repeated once more with ethyl acetate (20 ml). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a brown oily crude product. The crude product was purified by column chromatography (eluent: 100% dichloromethane → 90:10:1 dichloromethane:methanol:ammonia) to afford the target compound (S)-1-(5-bromopyridin-2-yl)pyrrolidin-3-ol as a white solid (1.0 g, 97% yield).1H NMR (400 MHz, CDCl3) δppm2.01-2.20 (m 3H), 3.41-3.60 (m, 4H), 4.58-4.61 (m, 1H), 6.23 (d, 1H), 7.45 (dd, 1H), 8.11 (d, 1H).LRMS m/z (APCI) 377 [MH+].

References

[1] Patent: US2008/85884, 2008, A1. Location in patent: Page/Page column 69
[2] Patent: US2009/88457, 2009, A1. Location in patent: Page/Page column 17
[3] Patent: US2009/62342, 2009, A1. Location in patent: Page/Page column 11
[4] Patent: US2009/176823, 2009, A1. Location in patent: Page/Page column 39
[5] Patent: WO2007/88514, 2007, A1. Location in patent: Page/Page column 104-105

(S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol(946002-90-0)Related Product Information

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